JPS61215335A - 脂環式化合物類の芳香族化合物類への転化方法 - Google Patents

脂環式化合物類の芳香族化合物類への転化方法

Info

Publication number: JPS61215335A
Authority: JP; Japan
Prior art keywords: compounds; hydrogen; alicyclic; compound; aromatic
Prior art date: 1985-03-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP61058474A

Other languages

English (en)

Japanese (ja)

Inventor

レズリー・ロバート・ルドニツク

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mobil Oil AS

Original Assignee

Mobil Oil AS

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-03-18

Filing date

1986-03-18

Publication date

1986-09-25

1986-03-18 Application filed by Mobil Oil AS filed Critical Mobil Oil AS

1986-09-25 Publication of JPS61215335A publication Critical patent/JPS61215335A/ja

Status Pending legal-status Critical Current

Links

150000001334 alicyclic compounds Chemical class 0.000 title claims description 29
150000001491 aromatic compounds Chemical class 0.000 title claims description 13
238000006243 chemical reaction Methods 0.000 title description 13
238000000034 method Methods 0.000 claims description 43
239000001257 hydrogen Substances 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 35
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
150000001875 compounds Chemical class 0.000 claims description 24
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 17
239000003054 catalyst Substances 0.000 claims description 15
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
239000011593 sulfur Substances 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
239000002243 precursor Substances 0.000 claims description 8
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 6
239000003208 petroleum Substances 0.000 claims description 6
239000007791 liquid phase Substances 0.000 claims description 4
150000003573 thiols Chemical class 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
150000002576 ketones Chemical class 0.000 claims 1
239000000852 hydrogen donor Substances 0.000 description 17
239000000370 acceptor Substances 0.000 description 16
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 10
125000003118 aryl group Chemical group 0.000 description 9
125000002723 alicyclic group Chemical group 0.000 description 7
-1 aliphatic thiol Chemical class 0.000 description 7
150000003464 sulfur compounds Chemical class 0.000 description 7
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 6
239000012965 benzophenone Substances 0.000 description 6
150000002430 hydrocarbons Chemical group 0.000 description 6
239000003921 oil Substances 0.000 description 6
239000000376 reactant Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
238000005899 aromatization reaction Methods 0.000 description 4
IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
SEXOVMIIVBKGGM-UHFFFAOYSA-N naphthalene-1-thiol Chemical compound C1=CC=C2C(S)=CC=CC2=C1 SEXOVMIIVBKGGM-UHFFFAOYSA-N 0.000 description 3
BYBPEZLZCGOWIS-UHFFFAOYSA-N perhydropyrene Chemical compound C1CC2CCCC(CC3)C2C2C3CCCC21 BYBPEZLZCGOWIS-UHFFFAOYSA-N 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
229920000049 Carbon (fiber) Polymers 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
239000004917 carbon fiber Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000003245 coal Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
239000000386 donor Substances 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000006574 non-aromatic ring group Chemical group 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
238000005504 petroleum refining Methods 0.000 description 2
SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
239000002002 slurry Substances 0.000 description 2
150000003871 sulfonates Chemical class 0.000 description 2
HSXSUCNPFUEKAJ-UHFFFAOYSA-N 1,1-dichlorohexylbenzene Chemical compound CCCCCC(Cl)(Cl)C1=CC=CC=C1 HSXSUCNPFUEKAJ-UHFFFAOYSA-N 0.000 description 1
MNXFZXVRYXNOBW-UHFFFAOYSA-N 1,2,3,3a,4,5,5a,6,7,8-decahydropyrene Chemical compound C1CCC2=CC=C3CCCC4C3=C2C1CC4 MNXFZXVRYXNOBW-UHFFFAOYSA-N 0.000 description 1
NHCREQREVZBOCH-UHFFFAOYSA-N 1-methyl-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene Chemical compound C1CCCC2C(C)CCCC21 NHCREQREVZBOCH-UHFFFAOYSA-N 0.000 description 1
XDFUNRTWHPWCKO-UHFFFAOYSA-N 4,5,9,10-tetrahydropyrene Chemical compound C1CC2=CC=CC3=C2C2=C1C=CC=C2CC3 XDFUNRTWHPWCKO-UHFFFAOYSA-N 0.000 description 1
WPCIUCNVWJNRCD-UHFFFAOYSA-N 4,5-dihydropyrene Chemical compound C1=CC=C2CCC3=CC=CC4=CC=C1C2=C34 WPCIUCNVWJNRCD-UHFFFAOYSA-N 0.000 description 1
FNMSYCARAJOBSC-UHFFFAOYSA-N 4-cyclohexylbutylbenzene Chemical compound C1CCCCC1CCCCC1=CC=CC=C1 FNMSYCARAJOBSC-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
150000001356 alkyl thiols Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000010504 bond cleavage reaction Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000005336 cracking Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003220 pyrenes Chemical class 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000003463 sulfur Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0217—Mercaptans or thiols
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
- C07C5/50—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with an organic compound as an acceptor
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
- C07C5/50—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with an organic compound as an acceptor
- C07C5/52—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with an organic compound as an acceptor with a hydrocarbon as an acceptor, e.g. hydrocarbon disproportionation, i.e. 2CnHp -> CnHp+q + CnHp-q

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pyridine Compounds (AREA)
Indole Compounds (AREA)

JP61058474A 1985-03-18 1986-03-18 脂環式化合物類の芳香族化合物類への転化方法 Pending JPS61215335A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US71321485A	1985-03-18	1985-03-18
US713214		1985-03-18

Publications (1)

Publication Number	Publication Date
JPS61215335A true JPS61215335A (ja)	1986-09-25

Family

ID=24865242

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61058474A Pending JPS61215335A (ja)	1985-03-18	1986-03-18	脂環式化合物類の芳香族化合物類への転化方法

Country Status (7)

Country	Link
EP (1)	EP0195541B1 (de)
JP (1)	JPS61215335A (de)
AT (1)	ATE35531T1 (de)
AU (1)	AU581498B2 (de)
BR (1)	BR8601173A (de)
DE (1)	DE3660361D1 (de)
ZA (1)	ZA861819B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2009085826A2 (en) *	2007-12-20	2009-07-09	Si Group, Inc.	Transhydrogenation processes
CN108311112B (zh) *	2018-03-16	2021-01-01	嘉兴学院	基于低温等离子体技术的表面巯基化碳纤维制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2953513A (en) *	1956-03-05	1960-09-20	Exxon Research Engineering Co	Hydrogen donor diluent cracking process
BE755817A (fr) *	1969-09-19	1971-03-08	Petro Tex Chem Corp	Procede de deshydrogenation oxydante favorisee par le soufre

1986
- 1986-02-19 AU AU53755/86A patent/AU581498B2/en not_active Ceased
- 1986-02-27 EP EP86301404A patent/EP0195541B1/de not_active Expired
- 1986-02-27 AT AT86301404T patent/ATE35531T1/de not_active IP Right Cessation
- 1986-02-27 DE DE8686301404T patent/DE3660361D1/de not_active Expired
- 1986-03-11 ZA ZA861819A patent/ZA861819B/xx unknown
- 1986-03-17 BR BR8601173A patent/BR8601173A/pt unknown
- 1986-03-18 JP JP61058474A patent/JPS61215335A/ja active Pending

Also Published As

Publication number	Publication date
BR8601173A (pt)	1986-11-25
ATE35531T1 (de)	1988-07-15
ZA861819B (en)	1987-10-28
AU5375586A (en)	1986-09-25
EP0195541B1 (de)	1988-07-06
AU581498B2 (en)	1989-02-23
DE3660361D1 (en)	1988-08-11
EP0195541A1 (de)	1986-09-24

Publication	Publication Date	Title
US2953513A (en)	1960-09-20	Hydrogen donor diluent cracking process
US3147206A (en)	1964-09-01	Hydrocracking process with the use of a hydrogen donor
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US4171260A (en)	1979-10-16	Process for reducing thiophenic sulfur in heavy oil
US3055956A (en)	1962-09-25	Process for the separation of naphthalene
US3223618A (en)	1965-12-14	Production of cracking feed stocks
JPS6315889A (ja)	1988-01-22	炭化水素混合物溶剤の製造方法
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US2383072A (en)	1945-08-21	Producing toluene
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EP0195541B1 (de)	1988-07-06	Verfahren zur Umwandlung alicyclischer Verbindungen in aromatische Verbindungen
Fainberg et al.	1997	Secondary pyrolysis of the products of the thermal destruction of high-sulfur oil shale
US3537982A (en)	1970-11-03	Method for hydrogenation
US2791541A (en)	1957-05-07	Two-stage hydrogen donor diluent cracking process
US3974063A (en)	1976-08-10	Denitrogenating and upgrading of high nitrogen containing hydrocarbon stocks with low molecular weight carbon-hydrogen fragment contributors
US3322843A (en)	1967-05-30	Treatment of paraffinic fractions
US2223133A (en)	1940-11-26	Treatment of petroleum products
US2409382A (en)	1946-10-15	Aviation gasoline production
US2927074A (en)	1960-03-01	Purification of hydrocarbon oils using sodium
US3177262A (en)	1965-04-06	Production of naphthalene